“Rich people analyze reward.

I’m doing the math and it seems to a lot of risk for not that much reward.

This is the mentality of people being created by rewarding these behaviors, she was convinced I would lie to the next landlord so as not to jeopardize her leaving my property peacefully, she was convinced enough to use me as a reference believing I would pass the buck down the road and screw the next person by giving her a good reference.

So yes, all can be done, just higher risk and potentially higher reward. 

Needless to say they were grateful.Point is, insurance is a cost that directly goes to your feelings on risk/reward. 

If you factor in your flood insurance, and the numbers still work, then you need to decide if the risk is worth the reward.

A complete gut job that ended up restoring a very old New England village Colonial to its original charm.

And when the market turns, they will drop you in a heartbeat and leave you with a mess.If you're going to let someone sublet/sublease your rental for a profit, you should only consider it if you can confirm they are professional and they are willing to share some of the profit and reward you for the increased risk.Personally, I would walk away and stick to your original investment plan.

In that case, I may determine market rates and raise them to 90% of that as a reward.

Works like a charm and there is no messy wax to clean up.